A waterfront promenade with multi-story buildings, palm trees, and a clear blue sky.

Vacation Rentals in Monroe County

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Top Cities in Monroe County

Our top choices for Monroe County vacation rentals

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (780 reviews)
"Such a great place to stay!!"
United States
Gavin
$123 nightly
The price is $138
Nov 10 - Nov 11
Total with taxes and fees
Breezy Palms Resort

2. Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,245 reviews)
"We had the pool view..Excellent!"
United States
Brandy
$111 nightly
The price is $122
Nov 29 - Nov 30
Total with taxes and fees
Knight's Key Suites

3. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (202 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
$304 nightly
The price is $342
Nov 10 - Nov 11
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina

4. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,013 reviews)
"The family running the food truck and tiki hut were great. Felt like we were guests in their home."
United States
Douglas
$119 nightly
The price is $134
Nov 10 - Nov 11
Total with taxes and fees
Tropical Cottages

5. Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club
3.0 star property
Key Largo
8.8 out of 10, Excellent, (352 reviews)
"Very clean Nice staff"
United States
Doris
$159 nightly
The price is $179
Nov 8 - Nov 9
Total with taxes and fees
Anchorage Resort & Yacht Club

6. Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (239 reviews)
"Never stayed in a houseboat before. It was a novel experience!"
United States
Susan
$243 nightly
The price is $273
Nov 15 - Nov 16
Total with taxes and fees
Aqua Lodge Rentals At Coconut Cay

7. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (180 reviews)
"Had a very enjoyable stay at Hemingway House. The place was spotless! All staff were very friendly and helpful. Would highly recommend staying here!"
United States
Diane
$254 nightly
The price is $286
Nov 9 - Nov 10
Total with taxes and fees
Treasure Harbor

8. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (380 reviews)
"Great view , clean room and excellent staff ( Mr. shaggy )"
United States
Jordan
$254 nightly
The price is $286
Nov 8 - Nov 9
Total with taxes and fees
Old Wooden Bridge Resort and Marina

9. Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,296 reviews)
"Great spot"
Canada
Justin
$201 nightly
The price is $226
Nov 8 - Nov 9
Total with taxes and fees
Skipjack Resort & Marina

10. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.6 out of 10, Exceptional, (380 reviews)
"Loved staying in the aqua lodges, such a relaxing place."
United States
Lauren
$231 nightly
The price is $259
Nov 8 - Nov 9
Total with taxes and fees
Yacht Haven Marina

11. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (43 reviews)
"great stay and value! glad we went with this place for our trip, everyone loved it! beautiful, clean and the pool was great too!"
Canada
Nick
$336 nightly
The price is $373
Nov 16 - Nov 17
Total with taxes and fees
Florida Keys Getaway - Slps 4 - Ocean View

12. Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!
Old Town Key West
9.6 out of 10, Exceptional, (463 reviews)
"This studio is in a wonderful location and comes with bikes and a pool spa. It is a fabulous place to stay for a relaxing get-away island-style."
United States
Laura D.
$236 nightly
The price is $262
Nov 18 - Nov 19
Total with taxes and fees
Steps from Duval, Pool on Site & Bikes Included!

13. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
2.5 star property
Marathon
9.2 out of 10, Wonderful, (147 reviews)
"It is an excellent place."
United States
Arianna
$220 nightly
The price is $247
Nov 30 - Dec 1
Total with taxes and fees
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

14. Piece of Paradise

Piece of Paradise
2.0 star property
Key largo
$355 nightly
The price is $377
Dec 1 - Dec 2
Total with taxes and fees
Piece of Paradise

15. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
$270 nightly
The price is $303
Nov 29 - Nov 30
Total with taxes and fees
Poolside Cottage #412

16. Ricky's Retreat - Truman @ Duval | Ideal Getaway!

Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Old Town Key West
9.8 out of 10, Exceptional, (40 reviews)
"Ricky’s Retreat is in a fantastic location. The room was all you need in Key West. Highly recommend it and will definitely stay there again."
United States
Brian R.
$341 nightly
The price is $381
Nov 16 - Nov 17
Total with taxes and fees
Ricky's Retreat - Truman @ Duval | Ideal Getaway!

17. SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (139 reviews)
"Great place to stay"
United States
walter l.
$325 nightly
The price is $361
Nov 10 - Nov 11
Total with taxes and fees
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

18. Aqua Lodges at 47th Street Gulfside

Aqua Lodges at 47th Street Gulfside
3.0 star property
Marathon
8.8 out of 10, Excellent, (61 reviews)
"Loved our stay at the aqua lodges 10/10 would do it again"
United States
Lauren
$270 nightly
The price is $303
Nov 29 - Nov 30
Total with taxes and fees
Aqua Lodges at 47th Street Gulfside

19. ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (115 reviews)
"Absolutely perfect! Great location, great property and great unit. Beautiful pool area with ice machine and filtered water dispenser was a highlight for the very hot and humid time we visited. Would return immediately and stay in the same spot. Thank you for a very enjoyable time in Key West!"
United States
Justin D.
$326 nightly
The price is $362
Dec 1 - Dec 2
Total with taxes and fees
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

20. Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (116 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
$332 nightly
The price is $368
Nov 19 - Nov 20
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Monroe County Hotel Reviews

Find out more about Monroe County

Discover your perfect Monroe County vacation rental with Expedia

How many vacation rentals are available in Monroe County?


Expedia has plenty of vacation rentals to choose from in and around  Monroe County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Monroe County?


The selection of Monroe County vacation rentals we have selected for you start as low as $122 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Monroe County?


Vacation rentals in Monroe County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Monroe County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Monroe County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Monroe County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Monroe County?


Find vacation rentals in Monroe County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Monroe County.  


What amenities are available in a vacation rental in Monroe County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Monroe County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Monroe County?   


Everytime is a great time to head to Monroe County! Staying in a Monroe County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Monroe County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Monroe County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Monroe County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Monroe County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.